Methyl 9-bromononanoate → 6-(N-Allyl-N-cyclohexylamino)-9-(8-methoxycarbonyloctyl)-purine

HRID 1721844

Reaktionsgleichung

Reaktionsgleichung von HRID 1721844
[Na].[CH2:2]([N:5]([C:12]1[N:20]=[CH:19][N:18]=[C:17]2[C:13]=1[NH:14][CH:15]=[N:16]2)[CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)[CH:3]=[CH2:4].Br[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([O:32][CH3:33])=[O:31]>CC(O)C>[CH2:2]([N:5]([C:12]1[N:20]=[CH:19][N:18]=[C:17]2[C:13]=1[N:14]=[CH:15][N:16]2[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([O:32][CH3:33])=[O:31])[CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]1)[CH:3]=[CH2:4]

Komponenten

5

Versuchsvorschrift

To a solution of 0.7 g. (30 mmole) sodium in 100 ml. propan-2-ol are added 7.7 g. (30 mmole) 6-(N-allyl-N-cyclohexylamino)-purine (compound of Example 8 j), the reaction mixture is heated to 40° C. for 10 minutes, 7.5 g. (30 mmole) methyl 9-bromononanoate are added thereto, the reaction mixture is heated under reflux for 16 hours and evaporated and the residue is taken up in water, extracted with dichloromethane, dried and evaporated. After chromatography on silica gel (elution agent: dichloromethane/methanol 95:5 v/v), there are obtained 4.8 g. of the title compound (37% of theory) in the form of an oil.

Aufarbeitung

  1. temperaturethe reaction mixture is heated
  2. temperatureunder reflux for 16 hours
  3. customevaporated
  4. extractionextracted with dichloromethane
  5. customdried
  6. customevaporated
  7. customAfter chromatography on silica gel (elution agent: dichloromethane/methanol 95:5 v/v), there are obtained 4.8 g

Quellen und Nachweise

ORD-Eintrag
ord-96d6df8cdf174eaeb41a244b4d4263ab
Quelldatensatz
uspto-grants-1989_08
Patentnummer
US04853386

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